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Mastering the Art of Proactive Communication

Our remote Executive Assistants are continually leveling up their skillset and toolbox. We have all-skate Dream Team Zoom Calls, we continually share new ideas and learnings in our private Slack community, we have periodic 1-1 coaching calls with our EAs to tackle specific challenges and we have cross-training (EA-to-EA) when it makes sense.

As a sample, here’s a bit of recent training we did to help our EAs know how to prompt our clients for additional work without pestering. 

As an executive assistant, there comes a point in every client relationship when the workload seems to slow down. Maybe it’s due to a vacation, a few disrupted weekly huddles (video calls), or other unforeseen circumstances. The reasons for a lull in work can vary, but one thing remains constant – you have the power to be proactive and keep the workflow flowing.

The challenge lies in finding the delicate balance between prompting for more work and avoiding the label of a persistent pest.

Your goal is clear: showcase your value as an indispensable asset to your client’s operations, not as a constant demand for attention.

Let’s explore how to master the art of prompting without pestering. 🚀

Step 1: Close Every Loop ✅

Before you even think about prompting for additional tasks or communication, make sure you’ve closed every loop your client has ever asked you to handle. Clients appreciate when tasks are not just completed but also neatly tied up. 🎁

Step 2: Create Your Cheat Sheet 📝

Keep a running list of tasks and projects you’ve successfully completed. Use this cheat sheet as your secret weapon to prompt without being pushy. Each accomplishment serves as a testament to your capabilities. 🌟

Step 3: Craft Thoughtful Questions ❓

When it’s time to prompt your client, use thoughtful questions that show you’re tuned into their needs and objectives. Here are some examples:

  • “In the past, I’ve helped you with events like X, Y, Z by ensuring you had A, B, C organized and ready. Do you have any events in the coming weeks or months that I can start working on?” 📅
  • “I’ve handled your travel arrangements around this time of year or season. Do you have any upcoming trips or events you’d like me to coordinate?” ✈️
  • “In previous projects, I’ve successfully managed X by doing Y. I think that worked really well. Do you have anything coming up on the horizon similar to X that I can take off your plate?” 📊
  • “I’ve noticed I have some increased capacity in my schedule. I’d love to devote it to supporting you even more effectively. Are there any areas where you’d appreciate additional assistance?” 🕒

Step 4: What Not to Say ❌

To avoid coming across as a pest, steer clear of phrases that may sound too demanding or vague:

  • “What do you need?”
  • “Do you have more tasks for me?”

Remember, the key is to demonstrate your proactive problem-solving abilities while respecting your client’s time and autonomy.

Prompting with finesse is an art, and when done right, you’ll be seen not as a burden but as a valuable partner dedicated to their success.

So, embrace the art of “PROMPT don’t PESTER,” and watch as you become an indispensable asset to your clients, ensuring that the workflow remains smooth and efficient. 🌐 🌟

Micah Foster headshot, Co-Owner of Dream Support for executive assistants

Micah Foster, Co-Owner

Micah Foster is a partner at Dream Support LLC who has been providing remote executive assistants to busy leaders who need administrative and organizational help for over five years.

He has a passion for creating and maintaining positive and productive work environments and empowering people to reach their full potential.